Interest in conversational intelligence has surged in recent years as evidenced by the ConvAI2 NeurIPS competition [1]}, [2]} and related efforts in natural language dialogue
[3]}. We build on prior Cyber-related dialogue work [4]}, focusing on critical conversational objectives beyond NLP-based cyber-attack detection and prediction [5]}, [6]}, [7]} or NLP-based generation of warnings and the explanations behind them [8]}. We implement a novel ask detection approach with the ultimate goal of sustaining a believable conversation with a social engineer to extract their true identity without putting valuable resources at risk.
